Playin’ Around With Playbook: Jesse Woolery

Hey everyone! After spreading #joyfuljazz with Denton High School, Sammy and I were eager to interview the band director responsible for it all: Jesse Woolery!. 

Jesse Woolery has served as the Associate Director of Bands and Director of Jazz Studies at Denton High School since 2007. He is the music caption head for the DHS Pride of Bronco Country Marching Band, directs the Symphonic Band, and guides all aspects of the jazz program which includes three full big bands and the newly formed DHS gospel ensemble. 

Woolery also is the Founder and Co-Director of the Chet Baker Educational Jazz Festival which is hosted each spring in Denton. As well as UIL success in both concert/ sight-reading and marching band, Mr. Woolery has directed groups from DHS at the Texas Music Educators Convention, Apex Jazz Festival, the University of North Texas Educational Leadership Conference, the Thinline Film Festival, and the Southwestern American Music Therapy Conference. 

Additionally, the jazz band has been selected as a main stage performer at the Jazz Education Network Conference, was a national finalist in the Swing Central Jazz Competition in conjunction with the Savannah Music Festival, and was the 2017 national commended winner of the Foundation for Music Education’s Mark of Excellence National Jazz Honors and named the National winners in 2016 and 2018.

We are so thrilled to continue Playbook clinics at Denton High School in the near future! 


Below is an excerpt from our conversation on January 13, 2022. Click here to view the full interview. 

TRISTA FORD: I know that you are the founder and co-director of the Chet Baker Educational Jazz Festival hosted in Denton each Spring. How did you go about building this festival from the ground up?

JESSE WOOLERY: I really wanted to have, not a big competitive festival, but one that’s really focused on education. When I started at Denton, I only had four students in our jazz band there, and it was almost like starting from scratch, even though there was jazz tradition there, all the way back to the 60s as a stage band. It kind of just went through the different directors, and you know they have different priorities and it almost became a theory class. Every single time these kids go to a jazz festival, they need an injection, a booster if you will. I had experiences where we would go to competitively ranked festivals, and kids have no idea really where they are at. Like “oh we’re 16th, what does that mean?” And kids kinda only get that out of it. So at ours, we have a big focus on the clinic afterward, getting a good recording for them, recognizing good soloists, etc. We just want everybody to walk away from the festival with really happy thoughts about it and want go back to their campuses wanting to do more.

TF: In terms of structuring a day at the jazz festival, how would it go for a band?

JW: I like that you ask this question, because of the educational focus I have right now, I wanted to get more clinic time. A lot of the time people come in and end up having too much setup time, or not enough playing time and they get done, and the clinician has nothing to say because they’ve got to move on. I’m giving everybody a 25-minute performance slot, and a clinic, and going into next year, we will have more clinics throughout the day.

TF: Why do you feel platforms like Playbook are so important in today’s classroom?

JW: Well,  I kind of see where a lot of these things are going, and there’s a lot of options in education for students. I’m a big public school believer, I’m a second-generation public school teacher, you know, honestly, my kids are elementary school age and my wife has been homeschooling them, and having [Playbook provide] supplements for this, for maybe a homeschool family, or maybe a place … like I mentioned, where there’s a small jazz program but the kid has got a love for jazz. When I met Sammy, Sam and Dave, and Ben, and all the guys, it was just a name to the face, because I felt like I’d already known them through the way of Playbook.


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